A resident black-tail deer walks the streets of Ashland, Oregon

Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"The residence was fantastic in every way. Me and my family enjoyed all the amenities and seeing the wildlife around the house outside. This place is a magical place! Thank you again! We will be back in the near future. "
United States
michael
The price is CA $279
CA $565 total
includes taxes & fees
Jun 25 - Jun 26
Grandview of Ashland

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Ashland
8.6 out of 10, Excellent, (4 reviews)
"Beautiful spot. Kind host."
United States
Lisa F.
The price is CA $271
CA $311 total
includes taxes & fees
Jun 13 - Jun 14
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
Jackson County
9.4 out of 10, Exceptional, (3 reviews)
"This was our second time staying at this cabin. Once again it was an amazing trip. We really enjoyed our quiet peaceful nights in the hot tub. Celebrated Thanksgiving there it was exactly what we wanted. Can’t wait for our next trip. "
United States
Taryn T.
The price is CA $207
CA $424 total
includes taxes & fees
Jun 15 - Jun 16
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

Homey Rustic Cabin in the Cascades

Homey Rustic Cabin in the Cascades
Jackson County
10.0 out of 10, Exceptional, (2 reviews)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is CA $223
CA $498 total
includes taxes & fees
Jun 15 - Jun 16
Homey Rustic Cabin in the Cascades

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"It was a nice family kind of place we loved it."
United Kingdom
Nicole F.
The price is CA $223
CA $442 total
includes taxes & fees
Jun 23 - Jun 24
Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Perfect huge Chateau territory! Clean rooms) quiet territory. The hosts are always available. "
United States
Irina
The price is CA $250
CA $353 total
includes taxes & fees
Jun 14 - Jun 15
Chateau Herb ~ Miranda Carriage House Apt

Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (16 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
The price is CA $225
CA $324 total
includes taxes & fees
Jun 15 - Jun 16
Chateau Herbe ~ Oberon Suite w/ Kitchen

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.4 out of 10, Exceptional, (8 reviews)
"Super nice place and great host what a gem"
United States
Robert
The price is CA $350
CA $453 total
includes taxes & fees
Jun 15 - Jun 16
Gorgeous Lakeside BarnHOUSE + SAUNA!

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
9.8 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is CA $188
CA $347 total
includes taxes & fees
Jun 15 - Jun 16
Charming carriage house in Ashland near downtown

Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"We had a great two-night stay. Beautiful home. No hair dryer, which was listed as an amenity, was a not so happy surprise."
United States
Vicki W.
The price is CA $306
CA $518 total
includes taxes & fees
Jun 16 - Jun 17
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is CA $319
CA $588 total
includes taxes & fees
Jun 14 - Jun 15
Savage Upon Siskiyou

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (63 reviews)
"Clean, comfortable and great location. We really enjoyed our stay and look forward to returning."
United States
Tonya W.
The price is CA $221
CA $416 total
includes taxes & fees
Jun 14 - Jun 15
Courtside Cottage - WalkScore 93 - Dog Friendly

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"My daughter lives in the area. Five adults stayed here for 3 nights. Beautiful location! Everyone loved the hot tub"
United States
Natalie N.
The price is CA $208
CA $422 total
includes taxes & fees
Jun 22 - Jun 23
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"If ever I were to own a cabin, it would be of the design of this one. Rustic feel with solid and complete foundational amenities. Greats: cathedral ceiling/loft/windows, large porch, bbq, wood stove, no TV, solid internet, great shower and bathroom, firm and comfortable mattresses. Nit-picky cons: jacuzzi isn't really a traditional hot tub, 30 min drive to/from Ashland on a very winding (yet picturesque) road, check-out time of 10am with $35 fee to extend to noon. Really enjoyed our stay, will...
United States
Eric M.
The price is CA $358
CA $689 total
includes taxes & fees
Jun 30 - Jul 1
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is CA $189
CA $318 total
includes taxes & fees
Jun 15 - Jun 16
Hanna's House by WanderLodges

Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort
Jackson County
10.0 out of 10, Exceptional, (1 review)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
The price is CA $251
CA $410 total
includes taxes & fees
Jun 29 - Jun 30
Cabin #4 at Hyatt Lake Resort

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is CA $188
CA $341 total
includes taxes & fees
Jun 15 - Jun 16
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (49 reviews)
"Len provided me with an outdoor table and extra chairs so I could have dinner outside with my family because one had the flu. So wonderful to be able to socialize with everyone without risking getting the flu! House was very comfortable and well supplied. Close to downtown and hiking. Off street parking for one car. Thank you so much!!!"
United States
Judy
The price is CA $146
CA $319 total
includes taxes & fees
Jun 15 - Jun 16
East Main Downtown Bungalow

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (225 reviews)
"Great spot, close to town, cozy and comfortable!"
United States
Carey C.
The Ashland Cottage, walk to town

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning property in the hills of Ashland!"
United States
Heather K.
The price is CA $305
CA $687 total
includes taxes & fees
Jun 25 - Jun 26
Hot tub | Sauna |Firepit |Sleeps 6!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and renowned opera this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!: This highly rated vacation home rental in Ashland has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Ashland include Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. and Gorgeous Lakeside BarnHOUSE + SAUNA!.

How many vacation rentals are there in Ashland?

Choose from 107 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Mount Ashland Ski Area are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.